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FridAI, AI Training + Claude Cowork – Business Brain 749 · Business Brain – The Entrepreneurs’ Podcast

• 0:00
  Dave Hamilton: Business Brain, episode 749 for Casual Friday AI, May 1st, National Executive
• 0:08
  Dave Hamilton: Coaching Day, and also National Phone-in Sick Day, 2026. Welcome back.
• 0:14
  Shannon Jean: I'm back. Those are kind of oxy-moron type, you know. Executive coaching,
• 0:18
  Shannon Jean: yes, go, go, go, and then call in sick.
• 0:20
  Dave Hamilton: Yeah, we probably spend too much time working, though. Like,
• 0:23
  Dave Hamilton: we probably need to call in sick more.
• 0:25
  Shannon Jean: No doubt, yeah.
• 0:26
  Dave Hamilton: Yeah, might be a good thing.
• 0:28
  Shannon Jean: Yes. I don't know. Maybe.
• 0:30
  Dave Hamilton: It's hard to know.
• 0:32
  Shannon Jean: Good to build systems so you don't have to work as much.
• 0:37
  Dave Hamilton: Exactly.
• 0:37
  Shannon Jean: But, yeah.
• 0:40
  Dave Hamilton: Greetings, folks, and welcome to Business Brain, the show where we take a few
• 0:44
  Dave Hamilton: ideas, we crunch them, we dissect them, we use them to tune our business brains
• 0:48
  Dave Hamilton: and lead even better charmed lives.
• 0:52
  Dave Hamilton: Our sponsor for this episode is Intuit QuickBooks Payroll at quickbooks.com slash workforce.
• 0:56
  Dave Hamilton: Things are evolving and expanding there. We'll talk more about that in a little bit.
• 1:00
  Dave Hamilton: For now, here in Durham, New Hampshire, I'm Dave Hamilton.
• 1:04
  Shannon Jean: And I'm Shannon Jean. I'm still in Northern California. How goes it, man? Happy Friday, I.
• 1:08
  Dave Hamilton: Happy Friday, I. I might phone in sick today because I've got Claude Cowork
• 1:14
  Dave Hamilton: doing a whole lot of stuff for me. Nice.
• 1:18
  Dave Hamilton: I've stumbled onto a new system, a new approach to using Claude Cowork.
• 1:26
  Dave Hamilton: Shannon, it turns out I'm Canadian. Yeah.
• 1:28
  Dave Hamilton: Oh, yeah. Okay. Yeah. They passed. Yeah. I found out on Friday.
• 1:33
  Dave Hamilton: They passed a law in Canada in December that I was unaware of until Friday that
• 1:40
  Dave Hamilton: says that if you have anyone in your lineage that was Canadian and you can prove it,
• 1:46
  Dave Hamilton: then you are a Canadian citizen.
• 1:49
  Dave Hamilton: Wow. Yeah. And so I don't currently, I don't need Canadian citizenship,
• 1:55
  Dave Hamilton: but that's exactly why I am going to go through the process and apply for it.
• 2:00
  Dave Hamilton: Because if I ever do, that's not the day to do it.
• 2:04
  Dave Hamilton: Yeah, that's right. And really, I am forming another business with a partner
• 2:09
  Dave Hamilton: and we are forming it as a Canadian corporation.
• 2:13
  Dave Hamilton: So there actually is a potential. Well, Canada has this whole,
• 2:17
  Dave Hamilton: like, you get a million and a quarter Canadian dollars of capital gains tax-free
• 2:25
  Dave Hamilton: throughout your life as a Canadian resident.
• 2:28
  Shannon Jean: Got it.
• 2:29
  Dave Hamilton: Not a citizen. Not a citizen. You've got to be a resident. Well,
• 2:32
  Dave Hamilton: the good news about Canadian citizenship, which is different from the U.S.,
• 2:36
  Dave Hamilton: is that Canada only taxes its residents on income, whereas U.S.
• 2:42
  Dave Hamilton: Taxes its citizens no matter where you live.
• 2:45
  Dave Hamilton: So yeah so there's like there's you know
• 2:48
  Dave Hamilton: there's some of that but there's a world where maybe it's
• 2:50
  Dave Hamilton: worth my while sometime down the road to have
• 2:54
  Dave Hamilton: you know i mean i would only have to live in canada for three months and
• 2:57
  Dave Hamilton: then i could be a resident and like if i there might be a tax benefit so i'm
• 3:00
  Dave Hamilton: gonna get the paperwork in place and it's been fascinating and of course not
• 3:04
  Dave Hamilton: only am i working with some of my family members several of whom have been going
• 3:08
  Dave Hamilton: nuts on genealogy recently for different reasons and so that's been really helpful
• 3:13
  Dave Hamilton: because a lot of this stuff just exists and
• 3:17
  Dave Hamilton: I started up a Claude Coworks session to kind of manage this process for me
• 3:21
  Dave Hamilton: because I got to collect all the data.
• 3:23
  Dave Hamilton: And then the most important part is writing a cover letter. And this is where
• 3:28
  Dave Hamilton: the lawyers that are doing this make their money.
• 3:30
  Dave Hamilton: Writing a cover letter that not only describes all of the information and why
• 3:34
  Dave Hamilton: it is the thing that qualifies you for the citizenship,
• 3:41
  Dave Hamilton: but also explaining the anomalies that people, that the examiner is bound to find.
• 3:46
  Dave Hamilton: Cause some of these things, like for me, it's my great grandfather who was born in Canada in 1882. Um,
• 3:53
  Dave Hamilton: There is no birth certificate for him. It's not that we can't find it.
• 3:57
  Dave Hamilton: It's that one was never created and nor was one created back in the day, back in the day.
• 4:03
  Dave Hamilton: Right. So we're looking at like church records and census things and like all these things.
• 4:07
  Dave Hamilton: And so explaining it all is, you know, you have to explain the anomalies.
• 4:12
  Dave Hamilton: And for my daughter, it turns out, I didn't realize this until yesterday.
• 4:16
  Dave Hamilton: My middle name is misspelled on her birth certificate.
• 4:19
  Dave Hamilton: Had no idea. Interesting. But that's the kind of thing like an examiner might find.
• 4:23
  Dave Hamilton: Now, if you tell them in advance, you're going to find this and here's why it's
• 4:26
  Dave Hamilton: OK. And you draw the lines.
• 4:28
  Dave Hamilton: Then they're like, OK, yeah, no problem. You know, hopefully.
• 4:30
  Dave Hamilton: So that I'll have Claude Cowork write that cover letter for me,
• 4:34
  Dave Hamilton: too. And it it has been collecting everything.
• 4:36
  Dave Hamilton: And it's been it's been like inhaling all of this stuff from Facebook groups
• 4:42
  Dave Hamilton: and Reddit groups where people have been talking about this for the last five months.
• 4:45
  Dave Hamilton: And so it like all of that stuff is great.
• 4:49
  Dave Hamilton: However, as Claude Cowork works, it runs on one machine. It doesn't run in your
• 4:54
  Dave Hamilton: cloud instance of Claude. It runs on a computer.
• 4:58
  Dave Hamilton: So I have my desktop computer in my office as the Claude Cowork computer with this session.
• 5:04
  Shannon Jean: Okay.
• 5:05
  Dave Hamilton: But that sits in my office. My laptop is, you know, on the couch with me.
• 5:10
  Dave Hamilton: Right. Yes. And so what I wound up doing, and I can screen share into the computer
• 5:14
  Dave Hamilton: in the office and obviously control that session.
• 5:18
  Dave Hamilton: But before I created the session, I was just talking in a session with Claude,
• 5:23
  Dave Hamilton: like, hey, does this Canadian Bill C3 really apply to me?
• 5:26
  Dave Hamilton: And it was like, tell me about your family, you know, blah, blah, blah. I did the thing.
• 5:30
  Dave Hamilton: And I started feeding it documents and it's like, OK, now is the time to create
• 5:34
  Dave Hamilton: the co-work session to do this.
• 5:36
  Dave Hamilton: And it gave me the prompt to do it. And I did. I started the co-work session.
• 5:39
  Dave Hamilton: But then because I'm still on the couch and like doing this stuff back and forth,
• 5:43
  Dave Hamilton: I'm using this like chat session in Claude as my sort of sanity checker, my partner,
• 5:53
  Dave Hamilton: my it's my it's the the co brains of the operation, if you will.
• 5:58
  Dave Hamilton: And we are then telling Claude Cowork, which has become the grunt of the operation, what to do.
• 6:06
  Dave Hamilton: Now, Claude Cowork can be the brains of the operation and spawn off its own
• 6:10
  Dave Hamilton: agents. It is certainly built to do that.
• 6:12
  Dave Hamilton: But what's really been cool is having these two separate sessions because it
• 6:17
  Dave Hamilton: allows me to sanity check.
• 6:20
  Dave Hamilton: And this is why people who set up their own agent systems way beyond what you
• 6:25
  Dave Hamilton: can currently do in the apps of Claude and, you know, like Claude Code and Claude
• 6:29
  Dave Hamilton: Cowork, they set up exactly this.
• 6:31
  Dave Hamilton: There's the one agent you talk with and then, you know, dozens or even hundreds
• 6:36
  Dave Hamilton: of spawn agents that are all very purpose-built on specific things,
• 6:41
  Dave Hamilton: one of which is the one that sanity checks the results that come in.
• 6:44
  Dave Hamilton: So to have this sanity checker that I am sort of working with,
• 6:50
  Dave Hamilton: I will always use Claude Cowork this way to kind of have this second agent that's
• 6:57
  Dave Hamilton: my partner in crime, if you will.
• 7:00
  Shannon Jean: And is it, is that chat you're having on your laptop, can it access what's going
• 7:05
  Shannon Jean: on in CoWork and see what's it, or how is it checking?
• 7:09
  Dave Hamilton: No, I am, I am, I'm passing data back and forth somewhat manually.
• 7:14
  Dave Hamilton: It can see the folder, right? I mean, I've pointed Claude CoWork as a folder.
• 7:19
  Dave Hamilton: That folder is sent to all my computers.
• 7:20
  Dave Hamilton: So it can see what's in the folder.
• 7:23
  Dave Hamilton: And and and one of the things in the folder is like a document tracker
• 7:26
  Dave Hamilton: because we're having to like you know i'm it's shocking
• 7:30
  Dave Hamilton: to me how much my family already has but there
• 7:32
  Dave Hamilton: are a few things like my my grandmother's birth
• 7:36
  Dave Hamilton: certificate no one has which is just
• 7:38
  Dave Hamilton: i mean it's fine i can write to the you know
• 7:41
  Dave Hamilton: the whatever the town in massachusetts and have them
• 7:44
  Dave Hamilton: send it to me which i'm which claude actually did for claude co-work did
• 7:47
  Dave Hamilton: that for me and you know paid them their three dollars or
• 7:50
  Dave Hamilton: whatever to send it to me but um but you
• 7:53
  Dave Hamilton: know it so it can like my chat session can can see that folder but it it also
• 8:00
  Dave Hamilton: is just asking me like okay have you thought about this has it thought about
• 8:03
  Dave Hamilton: this and it's just really nice to have two different things that are kind of
• 8:07
  Dave Hamilton: almost running in parallel but but really one kind of checking the other
• 8:12
  Shannon Jean: It's pretty cool. I like it. It is. I think it's great.
• 8:14
  Dave Hamilton: Yeah. I mean, the evolution of this will be when you can really do this all
• 8:19
  Dave Hamilton: in one thing where, to your point, it can see what you want it to see without
• 8:25
  Dave Hamilton: you having to kind of manually point things at each other.
• 8:29
  Shannon Jean: Yeah, that's right. That's coming sooner than later.
• 8:31
  Dave Hamilton: I think. Oh, very, very much sooner. Yeah. They're watching how they are using it internally.
• 8:36
  Dave Hamilton: They're watching how we are using it. and that's where Claude Cowork came from
• 8:40
  Dave Hamilton: was people using Claude Code to do non-coding things and they're like okay well
• 8:44
  Dave Hamilton: we can just call it something else like it doesn't matter yeah just yeah it's fine smart I love
• 8:48
  Shannon Jean: It it's a great idea.
• 8:49
  Dave Hamilton: Yeah it's fantastic it was it was a an idea born of necessity or of convenience
• 8:54
  Dave Hamilton: I should say not necessity but I love it it's just great to have these two things
• 8:58
  Dave Hamilton: back and forth so that's my
• 9:00
  Dave Hamilton: that's my AI advice for the week is think about how you can do that so yeah
• 9:05
  Shannon Jean: I want to chat I also want to talk about ways to learn AI for your small business. Very worthwhile.
• 9:14
  Dave Hamilton: I'm in. I want to do that. Awesome. What I do want to do right now is I want
• 9:19
  Dave Hamilton: to talk about our sponsors.
• 9:20
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• 9:27
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• 10:01
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• 10:20
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• 10:23
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• 10:26
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• 10:31
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• 10:35
  Dave Hamilton: Payroll for sponsoring this episode.
• 10:38
  Dave Hamilton: What's next? Awesome. Learning about how to learn about AI for your business.
• 10:42
  Shannon Jean: If you've never heard, there's a thing called the SBDC, Small Business Development Centers.
• 10:47
  Shannon Jean: There's about 1,000 of them or so across the country.
• 10:50
  Shannon Jean: It's part of the SBA, I believe. Okay, yeah. And they received a ton of funding
• 10:55
  Shannon Jean: to teach small business owners about AI.
• 11:00
  Shannon Jean: And I'll give you a great example. Huh. On May 20th, there's a work session,
• 11:08
  Shannon Jean: webinar training session called Get Found in the Age of AI,
• 11:12
  Shannon Jean: Generative Engine Optimization,
• 11:17
  Shannon Jean: GEO, which we used to focus on SEO, but you actually want to come up as a resource in ChatGPT.
• 11:24
  Dave Hamilton: Claude, Gemini, all these. One of my businesses, we get more referrals from
• 11:27
  Dave Hamilton: ChatGPT than any other source. Yeah.
• 11:31
  Shannon Jean: So that's on May 20th. On May 13th, coming up, just in a couple weeks,
• 11:35
  Shannon Jean: there's a session on AI-driven content creation to help you create content for
• 11:40
  Shannon Jean: your own site or socials or whatever.
• 11:42
  Shannon Jean: But there's over 1,000 of these offices, and you can find it at sbdcnet.org.
• 11:52
  Shannon Jean: And go search your state, and you'll find... A lot of them are online training,
• 11:55
  Shannon Jean: so it doesn't really matter what state you're in. Sure.
• 11:58
  Shannon Jean: These two I just mentioned are webinars. We're going to put the...
• 12:03
  Shannon Jean: Links in the show notes, so you can find it at businessbrain.show.
• 12:06
  Shannon Jean: But it was great. I was just kind of working with Claude.
• 12:08
  Shannon Jean: I was talking about, hey, I want to talk about what topics am I going to discuss?
• 12:12
  Shannon Jean: What's going on in the AI world this week?
• 12:16
  Shannon Jean: And this came up as one. I was like, man, this is a great resource,
• 12:18
  Shannon Jean: especially for small business owners that maybe they don't want to hire somebody
• 12:22
  Shannon Jean: to come do it. Maybe there's somebody on your staff that could learn how to do it.
• 12:26
  Shannon Jean: And these training things are great. I think they're pretty fascinating.
• 12:30
  Shannon Jean: And if you see the calendar.
• 12:33
  Dave Hamilton: Sbdcnet.org
• 12:34
  Shannon Jean: You got it is that right and you find your
• 12:37
  Shannon Jean: local one so you click like into California where I'm at and you can say okay
• 12:42
  Shannon Jean: there's 56 offices in California amazing which is amazing right and then you
• 12:50
  Shannon Jean: say okay on demand training they have live workshops and on demand training you can just take these,
• 12:57
  Shannon Jean: there's tons of stuff startup pre-planning accounting and then they've just added this AI on demand.
• 13:06
  Shannon Jean: Let me go back. They just added a whole slew of AI stuff.
• 13:12
  Shannon Jean: And I think it's awesome.
• 13:14
  Dave Hamilton: That's, I think that's awesome too. Oh man. Yeah.
• 13:17
  Shannon Jean: I just wanted to point out that resource, make sure that you,
• 13:19
  Shannon Jean: if you want to learn about more and diving into this stuff, go jump in and.
• 13:26
  Dave Hamilton: Teach yourself. I think that's worth it. Yeah. Yeah.
• 13:30
  Dave Hamilton: I like my excitement is genuine here. It sounds like yours is too, Shannon.
• 13:35
  Dave Hamilton: Like, even though we're trying to learn always like trying to teach how to use AI for your business.
• 13:42
  Dave Hamilton: The reason we get to teach this is in parallel, we are ravenously learning about this stuff.
• 13:48
  Dave Hamilton: So no one is an expert yet.
• 13:51
  Dave Hamilton: I mean, you might be an expert at different bits and pieces of it,
• 13:54
  Dave Hamilton: but I don't know that it will ever be possible.
• 13:56
  Dave Hamilton: To be an expert at all of it. It's certainly not currently possible.
• 13:59
  Dave Hamilton: So I love the idea that I can learn
• 14:02
  Shannon Jean: About this stuff. Yeah, and the other thing they offer is you can get an advisor
• 14:04
  Shannon Jean: and somebody who's had experience in business. They can help you out, somebody to talk to.
• 14:07
  Shannon Jean: Yes. But they have all kinds of these workshops. I mentioned a couple of them.
• 14:13
  Shannon Jean: There's just, like I say this, there's just over and over all through May that
• 14:17
  Shannon Jean: place government contracts, how to buy, how to sell your business. Love it.
• 14:23
  Shannon Jean: How to elevate your website image in video assets with AI. That is on May 21st.
• 14:28
  Shannon Jean: It's a 90-minute workshop. It doesn't cost anything.
• 14:31
  Dave Hamilton: Amazing.
• 14:32
  Shannon Jean: You should be over there watching it because what's going to happen is,
• 14:36
  Shannon Jean: or what's happening now is more and more small businesses are jumping in and
• 14:41
  Shannon Jean: adopting AI, whether it's agents answering your phone or helping in your workflow.
• 14:47
  Shannon Jean: One of the greatest things that I've ever had and ever used is an agent that
• 14:52
  Shannon Jean: creates drafts of every email and when I open up an email there is a draft ready
• 14:59
  Shannon Jean: to go and I can go edit it if I need to or I can often probably,
• 15:04
  Shannon Jean: 70% of the time I just said send and that's it it's.
• 15:08
  Dave Hamilton: I'm getting more and more emails that are clearly written by AI. And it's not, it's okay.
• 15:15
  Shannon Jean: Some stuff, yeah.
• 15:16
  Dave Hamilton: It's fine.
• 15:16
  Shannon Jean: A lot of times I just change. Okay,
• 15:18
  Shannon Jean: all right, let me just change this or whatever. But it certainly beats.
• 15:21
  Shannon Jean: And then using like WhisperFlow, which is life-changing, and Apple should totally buy them.
• 15:27
  Shannon Jean: Just being able to dictate it and make a quick change, it's terrific.
• 15:32
  Dave Hamilton: Love it.
• 15:32
  Shannon Jean: Really great. So if you get up here on whatever the URL that we mentioned earlier,
• 15:39
  Shannon Jean: if you go to businessbrain.show and grab it, come back and tell us.
• 15:42
  Shannon Jean: Tell us how you like the course, how it was, and if it's a good resource.
• 15:47
  Dave Hamilton: Amazing. I love it. Thanks for bringing that up. That's great, man.
• 15:52
  Shannon Jean: Just a quick tip. Building a lifelong curriculum makes a huge difference.
• 15:58
  Shannon Jean: Keeping your brain curious, especially as you build and get older, it's it's a game changer.
• 16:03
  Dave Hamilton: It's totally a game changer that that maintaining neuroplasticity
• 16:07
  Dave Hamilton: folks like it i i love when i get to learn new things and i make sure i do it
• 16:12
  Dave Hamilton: every single day so yeah thanks for hanging out this has been a good one fun
• 16:18
  Dave Hamilton: week and uh have a great weekend keep living that charmed life feedback at businessbrain.show
• 16:24
  Dave Hamilton: let us know what you think all right later see ya